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All-Weather Architecture & History Trek

Chicago, United States

Check local COVID-19-related recommendations or restrictions before booking.

In-person Airbnb Experiences are available in this region. Please review and follow local COVID-19-related recommendations or restrictions. Learn More

Experience hosted by Kelly

2 hours
Includes food, equipment
Up to 10 people
Hosted in English

What you'll do

We'll meet in an easy sheltered spot to discuss the tour and begin our way trekking through Chicago. We'll use the expansive city sidewalks, plazas, parks and Riverwalk as well as part of the underground Pedway system that is known to only a percentage of Chicagoans (we have 5 miles of Pedway!). We'll learn about the history of The Windy City (as well as why we're REALLY called The Windy City) while digesting some of our city's most prominent sights. Using some of the Loop's buildings and sculptures, we'll get rare, unique views and traverse the city like a local. If you're curious about Prohibition-era ganster lore or our speakeasy past, we can cover that too. Be prepared for indoor and outdoor walking as our trek will take us outside, especially during Covid for fresh air. Please let me know if you have any allergies or food sensitivities, as we’ll be stopping for an authentic Chicago snack that's been around for a century where they serve the city's best hot chocolate with an extra twist. Whether you're a local or this is your first visit, I promise to pack lots of interesting tidbits into our 2 hours together!
COVID-19 UPDATE: We're spending more time outside as there is PLENTY to see & keeping the groups small so we can practice safe social distancing. I have disinfecting wipes too.
We'll meet in an easy sheltered spot to discuss the tour and begin our way trekking through Chicago. We'll use the expansive city sidewalks, plazas, parks and Riverwalk as well as part of the underground Pedway system that is known to only a percentage of Chicagoans (we have 5 miles of Pedway!). We'll learn about the history of The Windy City (as well as why we're REALLY called The Windy City) while digesting some of our city's most prominent sig…

Kelly's commitment to safety

This host has committed to Airbnb’s COVID-19-related safety and cleaning guidelines – including adhering to social distancing guidelines, practising good hygiene, and ensuring that all participants wear a mask.
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What's included

  • Food
    We'll sample a local snack from a decades-old Chicago staple
  • Equipment
    I'll provide a rain poncho, should you need one
From £23
/ person
Sat, 5 Dec
11:30 - 13:30
£23 per person
£23 per person
Sun, 6 Dec
11:30 - 13:30
£23 per person
£23 per person
Mon, 7 Dec
10:00 - 12:00
£23 per person
£23 per person

Meet your host, Kelly

Host on Airbnb since 2014
  • 76 Reviews
  • Identity verified
I'm Kelly (a.k.a. ChiCitiGirl), a mapgeek, history enthusiast, architecture admirerer and food fanatic. I'm a trained city guide (5-star tours!) and I've been doing fun excursions for friends & family for decades. The Windy City has been my home for 26 years and I know how to get around to experience the best sights and bites. Working in the food and beverage industry for 10+ years has given me added insight into some of Chicago's hottest spots. I'm also a Chicago Architecture Center Open House volunteer, river kayak guide & Chicago History Museum member, using their library to research Chicago as well as the history of the 125+ year Victorian building I call home. I've traveled the world doing walking tours and know from personal experience how to make the best of our time together. I try to make a new friend every day, come play with me
I'm Kelly (a.k.a. ChiCitiGirl), a mapgeek, history enthusiast, architecture admirerer and food fanatic. I'm a trained city guide (5-star tours!) and I've been doing fun excursions for friends & family for decades. The Windy City has been my home for 26 years and I know how to get around to experience the best sights and bites. Working in the food and beverage industry for 10+ years has given me added insight into some of Chicago's hottest spots. I'm also a Chicago Architecture Center Open House…
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Where you'll be

I'll take you to see some of Chicago's prominent sights like The Chicago Theatre, Picasso Statue, City Hall, Daley Center and Plaza, Marina Towers, Riverwalk, Wrigley Building, Millenium Park and Cultural Center as well as a few things that are off-the-beaten-path. We'll view some some stunning interiors and artwork, all while learning what makes us The City That Works as well as some great stories about how things came to be.

Rated 5.0 out of 5 from 76 reviews.

Dillon
October 2020
AMAZING!!! My first Airbnb experience was so worth the money. I was hesitant about it but Kelly was so personable, friendly and knowledge about the city. You can tell she really enjoyed teaching me about Chicago and its architecture. It was a little cold and rainy, but I didn't mind at all as she is a great storyteller and I leaned 1000x more about Chicago than I would have on my own. Kelly absolutely sold me on the Airbnb experience!
AMAZING!!! My first Airbnb experience was so worth the money. I was hesitant about it but Kelly was so personable, friendly and knowledge about the city. You can tell she really en…
Elisabeth
October 2020
Kelly is an excellent guide and we learned a lot. We were happy with the small group size and everyone wore their masks.
Jordan
October 2020
Kelly's tour was everything we were hoping for! She provided such great information and presented in such a friendly welcoming way. We felt as if a good friend was giving us a walk around the city explaining things we never would have known about otherwise. A tremendous value. I highly recommend a tour with Kelly, hands down! Thanks Kelly!
Kelly's tour was everything we were hoping for! She provided such great information and presented in such a friendly welcoming way. We felt as if a good friend was giving us a walk…
Carol
October 2020
Excellent tour. We only had one day to discover Chicago, so Kelly’s tour was a great way to learn a lot in a short period of time. Very glad we signed up.
Liselle
September 2020
Kelly was absolutely amazing ! She’s knowledgeable, patient and welcoming. The tour took us to some great picture perfect spots. If you’re a history buff, appreciate architecture or just want to get to know the city in a short amount of time this tour for you.
Kelly was absolutely amazing ! She’s knowledgeable, patient and welcoming. The tour took us to some great picture perfect spots. If you’re a history buff, appreciate architecture o…
Léa
September 2020
Kelly was an amazing guide. I truly loved this unique experience. All the information she gave me was interesting and unique. She is really passionate about her city and know everything about it. She made us take the L and even offered original chocolates in the Fannie May boutique. The experience was even better than expected and she was truly interested in getting to know us and giving each of us the best experience of Chicago she could.
Kelly was an amazing guide. I truly loved this unique experience. All the information she gave me was interesting and unique. She is really passionate about her city and know every…

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Things to know

Cancellation policy

Any experience can be cancelled and fully refunded within 24 hours of purchase, or at least 7 days before the experience starts.

Guest requirements

Up to 10 guests ages 6 and up can attend.

What to bring

Please be prepared for the weather as we will be inside and out. Layers are recommended. Comfortable shoes are a must.